Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Patent
1990-02-27
1993-11-30
Killos, Paul J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
C07L 5948, C07L 6336
Patent
active
052667235
ABSTRACT:
A chemical process is disclosed for the preparation of a pharmaceutically active compound in an enantiomeric form either (R) or (S) of the structure ##STR1## and a suitable pharmaceutical salt, e.g. alkali or earth metal, D-glucamine or D-ribamine, where R.sub.1 represents an optionally substituted aryl group same as phenyl or naphthyl group, optionally including a heterocyclic ring system, which is optionally substituted, or represents a hetero-aromatic ring system optionally containing in addition to carbon atoms one or more atoms selected from the group consisting of nitrogen and oxygen; the enantiomeric R or S-compounds of (I) are obtained from a suitable ketone (II) by reduction with an LiAlH.sub.4.sup.- "chiraldid-complex" to the corresponding S- or R-alcohol, following chlorination with retention of configuration, and producing a steriochemical pure R or S magnesium organic compound by subsequent carbonation with carbon dioxide in the presence of a ligand by keeping the stereochemical configuration R or S at 98% enantiomeric excess at least including high yields, and if desired converting compounds (I) into a pharmaceutically acceptable salt or ester thereof. Especially pharmaceutically complexes with D-glucamine and D-ribamine in a stoichiometric ratio of 1:1, including salts comprised of N-cationic detergents with 2-(S)-aryl-alkanoic acids.
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Hanna Samir B.
Paradies Henrich H.
Schneider Bernd
Killos Paul J.
Medice, Ltd., Chem.-Pharm. Fabrik Putter GmbH & Co. KG
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